EP1596445B2 - Verfahren zur Dotierung von organischen Halbleitern mit Chinonderivaten - Google Patents
Verfahren zur Dotierung von organischen Halbleitern mit Chinonderivaten Download PDFInfo
- Publication number
- EP1596445B2 EP1596445B2 EP05008447.4A EP05008447A EP1596445B2 EP 1596445 B2 EP1596445 B2 EP 1596445B2 EP 05008447 A EP05008447 A EP 05008447A EP 1596445 B2 EP1596445 B2 EP 1596445B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- organic
- compound
- dopant
- group
- perfluoroalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title description 7
- 230000008569 process Effects 0.000 title description 6
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- 239000002019 doping agent Substances 0.000 claims abstract description 72
- 239000011159 matrix material Substances 0.000 claims abstract description 58
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- 238000001704 evaporation Methods 0.000 claims abstract description 27
- 230000008020 evaporation Effects 0.000 claims abstract description 26
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 26
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 23
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 239000002243 precursor Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 150000003254 radicals Chemical class 0.000 claims description 51
- -1 amidinformyl Chemical group 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 229910052720 vanadium Inorganic materials 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 150000004032 porphyrins Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000004059 quinone derivatives Chemical class 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 5
- 229910000071 diazene Inorganic materials 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000005259 triarylamine group Chemical group 0.000 claims description 3
- JMHMUBDZJWEILM-UHFFFAOYSA-N (4-cyanoimino-2,3,5,6,7,8-hexafluoronaphthalen-1-ylidene)cyanamide Chemical compound FC1=C(F)C(F)=C2C(=NC#N)C(F)=C(F)C(=NC#N)C2=C1F JMHMUBDZJWEILM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- FTOYXCYNGNXXQP-UHFFFAOYSA-N 5,10-dioxo-[1,4]dithiino[2,3-g][1,4]benzodithiine-2,3,7,8-tetracarbonitrile Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C(SC(=C(C#N)S1)C#N)=C1C2=O FTOYXCYNGNXXQP-UHFFFAOYSA-N 0.000 claims description 2
- FOGSGWDFZPLGFF-UHFFFAOYSA-N azanylidyne-[[nitro(nitroso)sulfamoyl]amino]methane Chemical compound C(#N)NS(=O)(=O)N(N=O)[N+](=O)[O-] FOGSGWDFZPLGFF-UHFFFAOYSA-N 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229920002098 polyfluorene Polymers 0.000 claims 1
- 229920006389 polyphenyl polymer Polymers 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract description 24
- 125000005843 halogen group Chemical group 0.000 abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 abstract description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 150000004053 quinones Chemical class 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
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- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 0 CC(C)=C(C(*)=C1*)c(c(*)c(C(C(C)=C(*)C2=*)=*)c2c2*)c2C1=N Chemical compound CC(C)=C(C(*)=C1*)c(c(*)c(C(C(C)=C(*)C2=*)=*)c2c2*)c2C1=N 0.000 description 6
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- 238000007254 oxidation reaction Methods 0.000 description 6
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000004997 halocarbonyl group Chemical group 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
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- 239000000460 chlorine Substances 0.000 description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- RHPVRWXUCDJURW-UHFFFAOYSA-N (4-cyanoiminocyclohexa-2,5-dien-1-ylidene)cyanamide Chemical class N#CN=C1C=CC(=NC#N)C=C1 RHPVRWXUCDJURW-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 229960000583 acetic acid Drugs 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 125000005427 anthranyl group Chemical group 0.000 description 1
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- 230000031709 bromination Effects 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
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- 150000003585 thioureas Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical group Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
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Classifications
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
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- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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Definitions
- the invention relates to the use of an organic mesomeric compound as an organic dopant for doping an organic semiconductive matrix material for changing the electrical properties thereof, an organic semiconductive material, a process for producing an organic semiconductive material and an electronic component with an organic semiconductive material.
- organic semiconductors can also be strongly influenced by doping with regard to their electrical conductivity.
- Such organic semiconductive matrix materials can be constructed from either compounds with good electron donating properties or from compounds having good electron acceptor properties.
- strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethyne (F4TCNQ) have become known.
- TCNQ tetracyanoquinonedimethane
- F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethyne
- Suitable matrix materials with hole transport properties are, for example, N, N'-perarylated benzidines TPD or N, N ', N "-perarylated starburst compounds, such as the substance TDATA, or else certain metal phthalocyanines, in particular zinc phthalocyanine ZnPc .
- Dicyanochinondiimine are known, which can be used as charge-transfer complexes (1: 1 complexes) or radical anion salts for potential organic metals.
- EP-A-0 061 264 describes tetracyanoanthraquinone dimethane compounds and processes for their preparation, polymers and charge-transfer complexes obtained therefrom.
- the compounds investigated so far have disadvantages in the production of doped semiconducting organic layers or of corresponding ones for a technical application electronic components with such doped layers, since the manufacturing processes in large-scale production plants or those on a pilot plant scale can not always be controlled with sufficient precision, which leads to high control and regulation effort within the processes to achieve a desired product quality, or to undesirable tolerances of the products .
- organic donors with respect to the electronic component structures such as light-emitting diodes (OLEDs), field effect transistor (FET) or solar cells themselves, since the mentioned production difficulties in handling the dopants to unwanted irregularities in the electronic components or unwanted aging effects of the electronic components being able to lead.
- the dopants to be used have suitable electron affinities and other properties suitable for the application, since, for example, the dopants also determine the conductivity or other electrical properties of the organic semiconductive layer under given conditions.
- the invention is therefore based on the object of providing organic dopants for doping organic semiconductors which are easier to handle in the production process and which lead to electronic components whose organic semiconducting materials can be produced in a reproducible manner.
- the object is achieved by the use according to claim 1, the organic semiconductive material according to claim 14, the method according to claim 15 and the electronic component according to claim 16.
- an organic mesomeric compound as organic dopant which is a quinone or quinone derivative, in particular an unsubstituted, substituted or fused quinone or quinone derivative, and the pure mesomeric compound under the same evaporation conditions has a lower volatility than tetrafluorotetracyanoquinone dimethyne (F4TCNQ), wherein the molar doping ratio of dopant to matrix molecule or monomeric unit of a polymeric matrix molecule is between 1: 5 and 1: 1000.
- F4TCNQ tetrafluorotetracyanoquinone dimethyne
- quinoid systems in particular quinoid systems are to be understood in which one, two or more quinoid oxygen atoms is / are replaced by a mesomerically and / or inductively electron-withdrawing, double bond-bound substituent, in particular by such a substituent specified below.
- Inductive electron-withdrawing are understood as meaning those radicals which, compared to carbon, have an -I effect, in particular unsaturated, hydrocarbon.
- the production processes can be better controlled and carried out with less effort and reproducible, with the provision of quinones or their derivatives as dopants these in the respective components with low diffusion coefficients, the same time Ensuring device structures, allow sufficient electrical conductivity of the organic semiconducting matrix with favorable electron affinity of the dopants.
- the dopants can be used to improve the charge carrier injection of contacts into the doped layer.
- the doped organic semiconductor material or the resulting electronic component can have improved long-term stability due to the compounds used according to the invention. This concerns, for example, a reduction of the dopant concentration with time.
- this relates to the stability of the doped layer disposed adjacent to undoped layers of an electro-optical device, so that electro-optical devices having increased long-term stability of electro-optical characteristics such as light output at a given wavelength, efficiency of a solar cell or the like result.
- the volatility may be measured here as the evaporation rate measured under the same conditions (for example a pressure of 2 ⁇ 10 -4 Pa and a predetermined evaporation temperature, for example 150 ° C.) or as vapor deposition rate of a substrate as layer thickness growth per unit time (nm / s) Conditions are determined.
- the volatility of the compounds according to the invention is preferably ⁇ 0.95 or 0.9 times, more preferably ⁇ 0.8 times, more preferably ⁇ 0.5 times, particularly preferably ⁇ 0.1 times or ⁇ 0.05 times or ⁇ 0.01 times F4TCNQ or less.
- the evaporation rate of the substrate with the compounds according to the invention can be determined, for example, using a quartz thickness monitor, as is commonly used, for example, in the production of OLEDs.
- the ratio of the vapor deposition rates of matrix materials and dopants can be measured by independent measurements thereof using two separate quartz thickness monitors to adjust the doping ratio.
- the volatility relative to that of F4TCNQ may refer respectively to that of the pure compound or to the volatility from a given matrix material, for example ZnPc.
- the compounds used in the invention are preferably such that they evaporate more or less or virtually undecomposed.
- targeting precursors as dopant sources which release the compounds used according to the invention, for example acid addition salts, for example a volatile or non-volatile inorganic or organic acid, or charge-transfer complexes thereof, wherein the acids or electron donors are preferably not or only slightly volatile or the charge-transfer complex itself acts as a dopant.
- the dopant is selected such that under otherwise identical conditions such as in particular doping concentration (molar ratio of dopant: matrix, layer thickness, current strength) for a given matrix material (for example, zinc phthalocyanine or another matrix material mentioned below) generates a precisely as high or preferably a higher conductivity as F4TCNQ, for example, a conductivity (S / cm) of greater than or equal to 1.1 times, 1.2 times or greater / equal to 1.5 times or twice that of F4TCNQ as a dopant.
- the dopant used in the invention is selected such that the doped with this semiconducting organic matrix material after a change in temperature of 100 ° C to room temperature (20 ° C) still ⁇ 20%, preferably ⁇ 30%, more preferably ⁇ 50% or 60% of Conductivity (S / cm) of the value at 100 ° C.
- one, two, three or four or all quinoids O groups of the quinoid compound, which may represent an ortho or para-quinoid system, which may also occur in polynuclear quinoid systems mixed ortho-para quinoid systems be selected from the group as below the substituents S0 to S11, S13 to S21 are defined, if appropriate also without S1, the substituents being defined below.
- one, two, three or four or more or all of the quinoid substituents of the quinoid system contain a mesomerically-linked -NO 2 and / or -C (O) R group.
- the compounds given may in each case comprise all stereoisomers, in particular syn and anti isomers, if these are each sterically possible.
- the substituents T, U, V, W, X, Y and Z are preferably mesomeric and / or based on carbon or a hydrocarbon, in particular a saturated hydrocarbon, inductive pulling double bond-bound substituents.
- the substituents 'T', U, V, W, X, Y and / or Z may each be different or the same and be selected from the group consisting of: wherein R is preferably an organic radical or hydrogen.
- R 17 can also be -CF 3 or perfluoroalkyl, in particular with C 1 -C 6.
- substituent is S17
- X and Y of the substituent S17 are preferably not again S17 and / or S18 to S21.
- the substituents T, U, V, W, X and / or Z may in particular be identical or different in the compounds 1-33 and be selected from the group consisting of wherein R is preferably an organic radical or hydrogen, wherein R17 of the group S8 in particular also -CF 3 or generally perfluoroalkyl, in particular with C1 to C6 be. In particular, one, two, three, four or all of the substituents may be selected from this group.
- X and Y may be the same or different and X or Y or X and Y may be selected from this group.
- V and W may be the same or different and V or W or V and W may be selected from this group.
- the substituents T, U, V, W, X, Y and / or Z in the compounds 1 to 33 may each be identical or different and be selected from the group consisting of wherein R is preferably an organic radical or hydrogen, wherein R17 of the group S8 also -CF3 or generally perfluoroalkyl, in particular C1 to C6 may be particularly. In particular, one, two, three, four or all of the substituents may be selected from this group.
- X and Y may be the same or different and X or Y or X and Y may be selected from this group.
- V and W may be the same or different and V or W or V and W may be selected from this group.
- the substituents T, U, V, W, X, Y and / or Z in the compounds 1 to 33 may each be identical or different and be selected from the group consisting of wherein R is preferably an organic radical or hydrogen, wherein R17 of the group S8 also -CF3 or generally perfluoroalkyl, in particular C1 to C6 may be particularly. In particular, one, two, three, four or all of the substituents may be selected from this group.
- X and Y may be the same or different and X or Y or X and Y may be selected from this group.
- V and W may be the same or different and V or W or V and W may be selected from this group.
- substituents T, U, V, W, X, Y and / or Z in the compounds 1 to 33 may be identical or different and be selected from the group consisting of S1, S5, S7-S9, S11, S14, S16-21, optionally also without S1, or from the group S1, S5, S8, S9, S11, S14, S16, S18, if appropriate also without S1.
- one, two, three, four or all of the substituents may be selected from this group.
- X and Y may be the same or different and X or Y or X and Y may be selected from this group.
- V and W may be the same or different and V or W or V and W may be selected from this group.
- the following substituent relationships may in particular apply to the group of the substituents S1 to S21.
- the following substituent relationships may apply to the group of substituents S1 to S11, S14 to S16.
- the following substituent relationships may apply to the group of substituents S1, S5-S14, S16.
- the following substituent relationships may apply to the group S3, S4, S6-S10, S15, S16.
- each of the substituents AA and BB are the same, they may also be different from each other.
- substituents in a quinoid compound, generally all quinoid substituents may be the same.
- X or Y or X and Y are not equal to O, in particular for the compounds or 1 or 20 or for compounds with only one quinoid ring.
- X or Y or X and Y are not equal to S, in particular for the compounds 1 or 20.
- the quinoid ring in particular if only one quinoidal ring is present, is preferably fused or substituted with at least one or at least two aryl radicals, of which one, several or all can also have heteroatoms.
- the substituents AA and / or BB are double-bond, mesomerically and / or inductively electron-withdrawing substituents, preferably selected from the group indicated below where appropriate, other suitable divalent, in particular double-bonded, substituents can be Solutionsstzt.
- R 28 can also be -CF 3 or another perfluoroalkyl group, preferably with C 1-6.
- the compound of the invention may be a quinoid system having a quinonoid ring and 1, 2 or 3 or more fused and / or each forming a radical R forming aromatic rings.
- the aromatic rings may each have one or more heteroatoms and be substituted or unsubstituted.
- the quinoid system may be an ortho or para-quinoid system.
- the quinoidal system may be selected, in particular, from the group of compounds 1-33, without being limited thereto to be.
- the invention further includes compounds having a quinoidal system of two rings each of 5 or 6 ring atoms, which can be fused with 1,2,3,4,5 or 6 or more aromatic rings and / or substituted to form a radical R.
- the aromatic rings may be substituted or unsubstituted.
- the rings preferably each have 6 atoms, which may be 6 carbon atoms.
- 1, 2, 3 or 4 or more C atoms can be replaced by heteroatoms such as O, S, N.
- Various quinoidal systems can be annealed, mesomerically linked, or otherwise linked through one or more double or triple bonds, which can be C-C bond or heteroatom C bonds.
- the compound may be selected from the group of compounds 1-33, without being limited thereto.
- the invention relates to compounds having 3 or 4 quinoid rings each independently 5 or 6 atoms, the 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 fused or a radical R forming aromatic rings with 6 Atoms may have.
- the aromatic rings may be substituted or unsubstituted.
- 1,2,3 or 4 atoms may be heteroatoms such as O, N or P.
- the compound may be selected from the group of compounds 1-33, without reference thereto to be limited.
- the compounds used according to the invention can have 1,2,3,4,5,6,7,8,9 or 10 aryl radicals, of which at least one, more or more preferably all with one or more quinoid systems and / or with one another are fused and / or the radicals R form.
- the aromatic rings may be substituted or unsubstituted.
- Aryl radicals should also be understood here as heteroaryl radical.
- the aryl radicals can each link two quinoidal rings, preferably with mesomeric linking of the quinoid rings.
- the quinone system may be selected from the group of compounds 1-33, without being limited thereto.
- R C
- M2 being the same and / or unequal and selected from the group -O-, -S-, -NR-.
- 2 or 3 or more (hetero) aryl rings can be arranged between the quinoid rings, bridging them.
- the compounds used according to the invention can have 2,3,4,5 or 6 or more quinoidal ring systems.
- one, several or all of the quinoid rings are 5- or 6-membered. Ring carbon atoms may be replaced by heteroatoms.
- At least two, several or all of the quinoid rings may be annealed to each other under mesomeric linkage to form a larger quinoid system, or mesomerically linked through one or more bridges, or not linked to form a larger mesomeric system.
- the compound may be selected from the group of compounds 1-33, without being limited thereto.
- the quinone system may be selected from the group of compounds 1-33, without being limited thereto.
- the radicals R 1 to R 32 may be identical or different and be selected from the group consisting of hydrogen, halogen, (in particular -F, -Cl), cyano, nitro, nitroso, sulfamide (unsubstituted or substituted, in particular C 1 -C 6 mono or di-alkyl substituted), carboxy, C1-C7 carbalkoxy, C1-C7 sulfo, sulfohalogen (especially -F or -Cl), halocarbonyl (especially F or -Cl), carbamoyl (unsubstituted or substituted, especially C1-C6 N monosubstituted or equal or independently N-C1-C6 disubstituted), formyl, amidinoformyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C25 hydrocarbon, preferably C1-C14 hydrocarbon or C1 to C10 or
- the hydrocarbon groups can each be especially perhalogenated, perchlorinated or perfluorinated (especially trifluoromethyl).
- the hydrocarbon groups may be linear or branched or cyclic, for example cyclohexyl or cyclopentyl.
- One or more carbon atoms may each be replaced by heteroatoms, in particular N, O, S, - (O) S (O) - or P (R).
- the (hetero) hydrocarbon radicals may be cyclically linked to one another or to a quinoid or other ring, for example a (hetero) aryl ring.
- the radicals R 1 to R 32 can be one of the groups acetyl, trifluoroacetyl, benzoyl, pentafluorobenzoyl, naphthoyl or alkoxycarbonyl, where the alkyl radical is an alkyl having one to six or ten, in particular up to four, unbranched or branched with one another may be connected carbon atoms, as well as trialkylphosphoryl with alkyl radicals, which may also consist of a chain with up to five or six or eight unbranched or branched or cyclically linked carbon atoms, or triarylphosphoryl with aryl radicals having preferably 6 to 14 carbon atoms, in particular to 10 C atoms.
- radicals R 1 - R 32 which may be the same or different, are either aryl or heteroaryl, such as phenyl, naphthyl, anthranyl, pyridyl, quinoxalyl, pyrazolyl, oxazolyl, 1,3,2-dioxaborinyl or 1,3 4 are oxdiazolyl which may be either hydrogen or a lower alkyl having from one to eight saturated carbon atoms which may be unbranched or branched or cyclic, but preferably halogen, with all fluorine or chlorine, trichloromethyl and perfluoroalkyl having one up to six carbon atoms, in particular trifluoromethyl, but also by cyano, nitro, nitroso, sulfo, carboxy, carbalkoxy, halocarbonyl, carbamoyl, formyl, amidinoformyl, alkylsulfanyl and alkylsulfony
- radicals R 2 , R 3 , R 4 , R 5 , R 6 in the compounds 3, 3b, 3c or formulas IV, V or VI may be the same or different for different n or m.
- the radicals R 1 to R 32 which are connected to a quinoid or aromatic system of a compound used in the invention and adjacent to each other and separated by two, three or four atoms of the quinoid or aromatic skeleton structure, can together to form a carbocyclic, especially aromatic ring , or heterocyclic, especially heterocarbocyclic ring. This applies in particular to the compounds 1 to 33, but also to other quinones or quinone derivatives used according to the invention.
- L can then be -O- or -S- or -NR-.
- two adjacent radicals of R 1 -R 32 can also be linked to one another via a carboxy- (CO) or a carbimide group (CNR) -, for which R the analogous substitution pattern applies as for R 1 -R 30 ,
- two adjacent radicals R are linked together via carbon atoms or heteroatoms such that a new carbocyclic or heterocyclic structural element is fused to the respective cyclic skeleton.
- halogen including preferably fluorine or Chloro, trifluoromethyl or cyano, nitro, nitroso, sulfo, carboxy, carbalk
- the bridged trans-diketoform of compound 8 may lead to structures 28 or 29 .
- the aromatic radicals with which the quinoid systems may be substituted and / or fused may be perhalogenated, in particular perfluorinated, perchlorinated or perfluorochlorinated.
- some, for example, up to one half or more of the halogen atoms may be replaced by hydrogen.
- CN groups may also be provided on the aromatic radicals and / or the quinoid systems.
- quinoid radicals Ch1 and Ch2 can be linked together via a radical ZB to form a compound Ch1-ZB-Ch2, where the quinoid radicals Ch1 and Ch2 can be mesomerically linked together or mesomerically independent of one another.
- the quinoid radicals Ch1 and Ch2 may be identical or different and may be selected from the group of compounds 1 to 4 and 5 to 33, it also being possible for further quinoidal systems to be linked to one another, for example with structures of structures such as Ch1-ZB1-Ch2 -ZB2-Ch3, wherein Ch1, Ch2, Ch3 may be the same or different and may respectively represent the compounds 1 to 4 and 5 to 33, without being limited thereto.
- ZB1 and ZB2 may be the same or different.
- the bridge -Z- can have 1, 2 to 4, to 6 or to 10 or even more bridging atoms, which can be carbon atoms or at least partially heteroatoms.
- this bridge -Z- may be unbranched from alkenylene, haloalkenylene, acetylene, alkylene, haloalkylene, in particular perfluoroalkylene having one to eight saturated carbon atoms or branched together, or arylene, hetarylene, which may either be hydrogen or lower alkyl radicals having from one to six or eight saturated carbon atoms, which may be unbranched or branched or cyclic, but preferably halogen, above all Fluorine or chlorine, trichloromethyl, perfluoroalkyl having one to six carbon atoms, in particular trifluoromethyl, but also cyano, nitro, nitroso, sulfo, carboxy, carbalkoxy, halocarbonyl, carbamoyl, formyl, amidinoformyl, alkylsulfanyl and alkylsul
- the alkenylene group and the alkylene group may have one or more CC multiple bonds.
- the bridging atoms of group Z may consist only of unsaturated carbon or heteroatoms, which groups may be unsubstituted or substituted.
- the bridging atoms of the group Z can consist only of saturated or aromatic carbon or heteroatoms, it being possible for the abovementioned groups to be unsubstituted or substituted, so that the two quinoid systems can be mesomerically linked to one another.
- the bridge -Z- may comprise one or more groups, in particular of the groups below, in the form of - (Z) n-, for example with n equal to 1, 2, 3 or 4 or more, each of which may be the same or different from each other.
- the radicals R 1 or R 2 may be different from the radicals R 1 or R 2 of the connecting base structures 1 to 33.
- 1,4-Quinones are best prepared by oxidation of the corresponding hydroquinones ( WT Summerford, DN Dalton, J. Am. Chem. Soc. 1944, 66, 1330 ; J. Miller, C. Vasquez, 1991 Patent US506836 ; K. Koch, J. Vitz, J. Prakt. Chem. 2000, 342/8 825-7 ) or fluorinated and / or chlorinated aromatics.
- N, N'-dicyan-1,4-quinonediimines are obtained by the action of N, N'-bistrimethylsilylcarbodiimide on 1,4-quinone compounds ( A. Aumüller, S. Hunig, Liebigs Ann. Chem., 1986, 142-64 ,) or by oxidation of corresponding N, N'-dicyan-1,4-diamine compounds ( GD Adreetti, S. Bradamante, PC Pizzarri, GA Pagani, Mol. Cryst. Liq. Cryst.
- N, N'-dicyano-1,4-diamine compounds can be obtained by cyanation of phenylene-1,4-diamine with cyanogen halides or by desulfurization of corresponding thiourea derivatives.
- Simple tetracyanoquinonedimethanes can be prepared via the 1,4-cyclohexanedione by condensation in benzene with ammonium acetate buffer on a water separator and subsequent oxidation by bromine ( DS Acker, WR Hertler, J. Am. Chem. Soc. 1962, 84, 3370 ). Furthermore, Hertier and co-workers have also shown that these compounds can be synthesized via 1,4-xylene and its analogues by side chain bromination, substitution by means of cyanide, condensation with diethyl carbonate, conversion of the carboxylic acid methyl ester groups into cyanide groups and subsequent oxidation ( J. Org. Chem. 1963, 28, 2719 ).
- Acceptor-substituted tetracyanoquinonedimethanes can be prepared from the sodium salt of t-butyl malononitrile and acceptor substituted 1,4-dihaloaromatic ( RC Wheland, EL Martin, J. Org. Chem., 1975, 40, 3101 ).
- Bridged quinoid compounds are represented by M. Matsuoka, H. Oka, T. Kitao, Chemistry Letters, 1990, 2061-4 ; J. Dieckmann, WR Hertler, RE Benson, JACS 1963, 28, 2719-24 ; K. Takahashi, S. Tarutani, JCS Chem. Comm. 1994, 519-20 ; NN Voroshzov, WA Barchash, Dokady Akad. SSSR 1966, 166/3, 598 ,
- Pyrazino-TCNQ compounds can be palladium-catalyzed via 5,8-diiodoquinoxalines with the sodium salt of malononitrile. ( T. Miyashi et al, J. Org. Chem. 1992, 57, 6749-55 )
- Pyrazino-TCNQ compounds as well as other heteroannulated derivatives can be prepared in various ways ( Y. Yamashita at al Chemistry Letters, 1986, 715-8 . Wudl et al., J. Org. Chem. 1977, 421656-7 ).
- Annuned DCNQI compounds can be synthesized via the corresponding quinones according to Hünig ( J. Tsunetsugu et al, Chemistry Letters, 2002, 1004-5 ).
- Heteroannulated DCNQI compounds can be synthesized via the corresponding quinones according to Hünig ( T. Suzuki et al, J. Org. Chem. 2001, 66, 216-24 ; N. Martin at al, J. Org. Chem. 1996, 61, 3041-54 ; K. Kobayashy et al, Chemistry Letters, 1991, 1033-6 ; K. Kobayashy, K. Takahashi, J. Org. Chem. 2000, 65, 2577-9 ).
- Heterocyclic quinoid derivatives can be prepared according to NF Haley, JCS Chem. Comm. 1979, 1031 . F. Weydand, K. Henkel Chem. B. 1943, 76, 818 ; HJ Knackmuss Angew. Chem. 1973, 85, 16 ; K. Fickentscher, Chem. B 1969, 102, 2378-83 . DE Burton at al. J. Chem. Soc. (C) 1968, 1268-73 ,
- Tetraacetylquinone methane compounds or their reduced forms are available via 1,4-benzoquinone and acetylacetone ( J. Jenik, Chemicky Prumysl 1985 35/60 1547 . RJ Wikholm J. Org. Chem. 1985, 50, 382-4 ; E. Bernatek, S. Ramstad Acta Chem. Scand. 1953, 7, 1351-6 ).
- Ditrifluoroacetamides can be prepared by means of trifluoroacetic acid via aromatic 1,4-diamines ( R. Adams, JM Stewart JACS 1952,20, 3650-4 ). By oxidation with Pb (IV) acetate, the diimine can be obtained.
- suitable dopants are described for organic semiconductive materials, such as hole transport materials HT , which are commonly used in OLEDs or organic solar cells.
- the semiconductive materials are preferably intrinsically hole-conducting.
- quinone-type dopants of the invention the following may apply.
- the matrix material may be partially (> 10 or> 25 wt%) or substantially (> 50 wt% or> 75 wt%)) or completely consist of a metal phthalocyanine complex, a porphyrin complex, in particular a metal porphyrin complex, an oligothiophene, oligophenyl, oligophenylenevinylene or oligofluorene compound, the oligomer preferably having 2-500 or more, preferably 2-100 or 2-50 or 2-10 comprises monomeric units.
- the oligomer may also comprise>4,> 6 or> 10 or more monomeric units, in particular also for the ranges indicated above, ie for example 4 or 6-10 monomeric units, 6 or 10-100 monomeric units or 10-500 monomeric units ,
- the monomers or oligomers may be substituted or unsubstituted, wherein block or copolymers may be present from said oligomers, a compound having a triarylamine unit or a spiro-bifluorene compound.
- the matrix materials mentioned can also be present in combination with one another, if appropriate also in combination with other matrix materials.
- the matrix materials may have electron donating substituents such as alkyl or alkoxy moieties which have reduced ionization energy or reduce the ionization energy of the matrix material.
- the metal phthalocyanine complexes or porphyrin complexes used as the matrix material may have a main group metal atom or a subgroup metal atom.
- the phthalocyanine complex or porphyrin complex may each be partially hydrogenated, but preferably the mesomeric ring system is not disturbed.
- the same or different metal atoms or oximetal atoms may be present in the case of porphyrin complexes.
- such dosable hole transport materials may include HT- arylated benzidines, for example N, N'-perarylated benzidines or other diamines such as TPD (where one, several or all of the aryl groups may have aromatic heteroatoms), suitable acrylated starburst compounds such as N, N ', N "-perarylated starburst compounds, such as the compound TDATA (wherein one, several or all of the aryl groups may have aromatic heteroatoms.)
- the aryl radicals may in particular for each of the above-mentioned compounds phenyl, naphthyl, pyridine, quinoline, isoquinoline, peridazine, pyrimidine , Pyrazine, pyrazole, imidazole, oxazole, furan, pyrrole, indole or the like
- the phenyl groups of the respective compounds may be partially or completely replaced by thiophene groups.
- the matrix material used consists entirely of a metal phthalocyanine complex, a porphyrin complex, a compound having a triarylamine unit or a spiro-bifluorene compound.
- the doping can be carried out in particular such that the molar ratio of matrix molecule to dopant or, in the case of oligomeric matrix materials, the ratio of matrix monomer number to dopant 1: 5 to 1: 1000, for example 1:10 to 1: 100, for example about 1:50 to 1: 100 or 1:25 to 1:50.
- the doping can be carried out in such a way that the dopant is evaporated out of a precursor compound which releases the dopant on heating and / or irradiation.
- the irradiation can be effected by means of electromagnetic radiation, in particular visible light, UV light or IR light, for example, in each case laser light, or else by other types of radiation.
- the irradiation can essentially provide the heat necessary for the evaporation, it can also be targeted to certain bands of the compounds or precursors to be vaporized or compound complexes such as charge-transfer complexes are irradiated, for example, to facilitate the evaporation of the compounds by dissociation of the complexes by conversion into excited states. It is understood that the evaporation conditions described below are directed to those without irradiation and for comparison purposes uniform evaporation conditions are used.
- the dopants according to the invention can be used for the production of organic light-emitting diodes (OLEDs), organic solar cells, organic diodes, in particular those with a high rectification ratio such as 10 3 -107, preferably 10 4 -10 7 or 10 5 -10 7 or organic field-effect transistors.
- OLEDs organic light-emitting diodes
- the dopants according to the invention can be used to improve the conductivity of the doped layers and / or to improve the charge carrier injection of contacts into the doped layer.
- the component may have a pin structure or an inverse structure, without being limited thereto.
- the use of the dopants according to the invention is not limited to the above-mentioned advantageous embodiments.
- the compounds to be used according to the invention in particular the compounds exemplified above by way of example of the above-described class of quinones, are now described in US Pat used as dopants for various hole conductors in the following manner, which in turn are used for the construction of certain microelectronic or optoelectronic devices, such as an OLED.
- the dopants can be simultaneously evaporated side by side with the hole transport materials of the matrix under high vacuum (about 2 ⁇ 10 -4 Pa) at elevated temperatures.
- a typical substrate evaporation rate for the matrix material is 0.2 nm / s (density about 1.5 g / cm 3 ).
- the evaporation rates for the dopants can vary between 0.001 and 0.5 nm / s with the same assumed density, in each case corresponding to the desired doping ratio.
- the evaporation temperatures of the compounds are given in a Substratbedampfungs worn, wherein F4TCNQ under otherwise identical conditions has an evaporation temperature of 80 ° C in order to deposit the same predetermined time unit (eg five seconds) an equal layer thickness (eg 1 nm) on the substrate, such as the dopants used in the invention.
- the evaporation temperature T (evap.) Is 85 ° C.
- the two components matrix and dopant were evaporated in a ratio of 50: 1 in vacuo.
- the conductivity is 2.4 ⁇ 10 -2 S / cm.
- the evaporation temperature T (evap.) Is 114 ° C.
- the ratio of the two compounds in the vapor-deposited layer is 1:50 in favor of the matrix.
- a conductivity of 1.0 ⁇ 10 -2 S / cm was measured.
- the evaporation temperature T (evap.) Is 118 ° C.
- the layer was evaporated in a ratio of 1:25 (dopant: matrix) in vacuo. In this case, a conductivity of 4.9 ⁇ 10 -4 S / cm was measured.
- Layer thickness (nm) Amperage (nA) Layer thickness (nm) Amperage (nA) 5 1.1648 55 66012 10 4.7852 60 74335 15 9.7211 65 82449 20 15582 70 90251 25 21985 75 97968 30 28866 84 106.14 35 35.45 85 114.58 40 42249 90 122.84 45 49747 95 131.1 50 57.86 100 139.59
- the evaporation temperature T (evap.) Is 122 ° C.
- Dotand and matrix were vapor-deposited in a ratio of 1:25 onto the support in vacuo. In this case, a conductivity of 2 ⁇ 10 -3 S / cm was achieved.
- Layer thickness (nm) Amperage (nA) Layer thickness (nm) Amperage (nA) 5 6.4125 55 300.85 10 26764 60 333.18 15 52096 65 365.28 20 79286 70 397.44 25 107.22 75 431.58 30 135.36 80 464.29 35 165.63 85 498.18 40 199.68 90 529.63 45 234.01 95 560.48 50 267.59 100 590.82
- the evaporation temperature T (evap.) Is 170 ° C.
- the layer was evaporated in a ratio of 1:25 (dopant: matrix) in vacuo. In this case, a conductivity of 4.5 ⁇ 10 -4 S / cm was measured.
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EP1596445B2 true EP1596445B2 (de) | 2015-09-30 |
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Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
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EP04002303A Expired - Lifetime EP1538684B1 (de) | 2003-12-04 | 2004-02-03 | Verfahren zur Dotierung von organischen Halbleitern mit Dioxaborinderivaten |
EP09002596A Withdrawn EP2083458A1 (de) | 2003-12-04 | 2004-02-03 | Organische mesomere Verbindungen als Dotanden |
EP10176990A Withdrawn EP2270894A1 (de) | 2003-12-04 | 2004-02-03 | Verwendung von organischen mesomeren Verbindungen als Dotanden |
EP05008447.4A Expired - Lifetime EP1596445B2 (de) | 2003-12-04 | 2004-02-03 | Verfahren zur Dotierung von organischen Halbleitern mit Chinonderivaten |
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EP04002303A Expired - Lifetime EP1538684B1 (de) | 2003-12-04 | 2004-02-03 | Verfahren zur Dotierung von organischen Halbleitern mit Dioxaborinderivaten |
EP09002596A Withdrawn EP2083458A1 (de) | 2003-12-04 | 2004-02-03 | Organische mesomere Verbindungen als Dotanden |
EP10176990A Withdrawn EP2270894A1 (de) | 2003-12-04 | 2004-02-03 | Verwendung von organischen mesomeren Verbindungen als Dotanden |
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US (2) | US6908783B1 (ko) |
EP (4) | EP1538684B1 (ko) |
JP (2) | JP2005167175A (ko) |
KR (1) | KR100622179B1 (ko) |
CN (1) | CN100530742C (ko) |
AT (2) | ATE442674T1 (ko) |
CA (1) | CA2462745C (ko) |
DE (3) | DE10357044A1 (ko) |
HK (2) | HK1078988A1 (ko) |
IN (2) | IN2004MU00382A (ko) |
TW (1) | TWI276142B (ko) |
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EP4333591A1 (en) | 2022-08-30 | 2024-03-06 | Novaled GmbH | Organic electroluminescent device comprising a compound of formula (i) and a compound of formula (ii), and display device comprising the organic electroluminescent device |
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- 2004-02-28 KR KR20040013756A patent/KR100622179B1/ko active IP Right Grant
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Also Published As
Publication number | Publication date |
---|---|
HK1082839A1 (en) | 2006-06-16 |
KR100622179B1 (ko) | 2006-09-08 |
US20050121667A1 (en) | 2005-06-09 |
HK1078988A1 (en) | 2006-03-24 |
DE502004010037D1 (de) | 2009-10-22 |
ATE417366T1 (de) | 2008-12-15 |
US20050139810A1 (en) | 2005-06-30 |
EP1538684A1 (de) | 2005-06-08 |
IN2004MU00382A (ko) | 2006-09-29 |
CA2462745C (en) | 2010-06-01 |
TWI276142B (en) | 2007-03-11 |
EP2270894A1 (de) | 2011-01-05 |
KR20050054427A (ko) | 2005-06-10 |
EP1596445B1 (de) | 2009-09-09 |
CN100530742C (zh) | 2009-08-19 |
IN2005MU01652A (ko) | 2007-12-21 |
DE502004008632D1 (de) | 2009-01-22 |
EP2083458A1 (de) | 2009-07-29 |
JP5465940B2 (ja) | 2014-04-09 |
CN1624948A (zh) | 2005-06-08 |
EP1538684B1 (de) | 2008-12-10 |
ATE442674T1 (de) | 2009-09-15 |
EP1596445A1 (de) | 2005-11-16 |
JP2010021554A (ja) | 2010-01-28 |
US6908783B1 (en) | 2005-06-21 |
JP2005167175A (ja) | 2005-06-23 |
CA2462745A1 (en) | 2005-06-04 |
DE10357044A1 (de) | 2005-07-14 |
TW200520020A (en) | 2005-06-16 |
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